87106-27-2

Basic information

• Product Name: (S)-2-methyl-1-phenylsulfonylbutane
• Synonyms: (S)-2-methyl-1-phenylsulfonylbutane
• CAS NO: 87106-27-2
• Molecular Weight: 212.313
• Mol File: 87106-27-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (S)-2-methyl-1-phenylsulfonylbutane(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-methyl-1-phenylsulfonylbutane(87106-27-2)
• EPA Substance Registry System: (S)-2-methyl-1-phenylsulfonylbutane(87106-27-2)

Safety Data

• Hazardous Substances Data: 87106-27-2(Hazardous Substances Data)

Upstream product

• 3112-85-4 methylphenylsulfonate 
• 61530-30-1 (R)-sec-butyl 4-methylbenzenesulfonate 
• 50896-54-3 (S)-(+)-1-methylpropyl p-toluenesulfonate 
• 87106-25-0 (R)-(+)-1-iodo-2-methylbutane 
• 16958-25-1 (R)-3-methylpentanoic acid 
• 152426-80-7 C₁₇H₂₀O₄S₂ 
• 94807-84-8 (S)-3-Methyl-4-phenylsulfanyl-butyric acid ethyl ester 
• 94807-95-1 Methanesulfonic acid (S)-3-methyl-4-phenylsulfanyl-butyl ester 
• 94807-93-9 (S)-3-methyl-4-phenylthio-1-butanol 
• 78505-05-2 (3S)-3-methyl-4-phenylsulfonylbutanol 
• 94807-80-4 Methanesulfonic acid (S)-4-benzenesulfonyl-3-methyl-butyl ester 
• 82363-37-9 ((S)-2-Methyl-butylsulfanyl)-benzene 
• 87144-80-7 methyl (R)-(+)-7-hydroxy-3,7-dimethyl-5-octenoate 
• 79936-62-2 methyl (3R)-3-methyl-5-oxopentanoate 

Downstream Products

• 87106-30-7 (3R,7R)-3,7-dimethylnonyl tosylate 
• 71777-34-9 (R)-(-)-10-methyl-1-dodecanol acetate 
• 87106-28-3 (3R,7R)-3,7-dimethyl-6-benzenesulfonylnonyl benzyl ether 
• 91787-38-1 2-methyl-1-phenylsulphonyl-1-trimethylsilylbutane 

Relevant articles and documents

Synthesis of four stereoisomers of (S)-2-methylpent-3-yl 3,13-dimethylpentadecanoate, a sex pheromone of the bagworm moth clania variegate, using stereospecific inversion of secondary sulfonates as a key step

Females of some lepidopteran species produce novel sex pheromones with a methyl-branched structure, such as 2-methylpent-3-yl 3,13-dimethylpentadecanoate secreted by the bagworm moth Clania variegate. Recently, we have established a simple preparative method for the synthesis of methyl-branched building blocks by utilizing an SN2 reaction of chiral secondary tosylates derived from (S)- and (R)-propylene oxides. The usefulness of these building blocks was demonstrated by their application in the synthesis of all four stereoisomers of an acid moiety in the bagworm pheromone. The enantiomeric purities of all building blocks were confirmed by enantioselective HPLC analysis. We found that a secondary mesylate was superior to the corresponding tosylate because it avoided an elimination side reaction, and racemization in the SN2 reaction was not observed even at high temperature (150 °C). Finally, each optically active acid was esterified with (S)-2-methyl-3-pentanol, which was synthesized by a new route starting from (S)-valine. A simple route to methyl-branched building blocks has been developed by utilizing an S N2 reaction of chiral secondary sulfonates derived from (S)- and (R)-propylene oxides. The usefulness of these building blocks was demonstrated by the stereospecific synthesis of all four stereoisomers of a bagworm pheromone. Copyright

A CONVENIENT SYNTHESIS OF (S)-2-METHYL AND (2S)-2,3-DIMETHYL BUTYL PHENYLSULFONES FROM (S)-(-)-3-METHYL-γ-BUTYROLACTONE

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